CHIRAL PHOSPHORIC ACID CATALYZED ASYMMETRIC FRIEDEL-CRAFTS ALKYLATION OF INDOLES WITH NITROOLEFINS

被引：9

作者：

Tang, Hong-Ying ^{[1
]}

Zhang, Zhong-Biao ^{[1
]}

机构：

[1] Tianjin Normal Univ, Tianjin Key Lab Water Environm & Resources, Tianjin 300387, Peoples R China

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2011年 / 186卷 / 10期

关键词：

Asymmetric Friedel-Crafts alkylations; enantioselectivities; chiral phosphoric acid; indoles; nitroolefins; TETRAHYDRO-BETA-CARBOLINES; BOND-FORMING REACTIONS; BRONSTED ACID; ENANTIOSELECTIVE ADDITION; NITROALKENES; COMPLEXES; IMINES; ORGANOCATALYSTS; BIS(OXAZOLINE); DISCOVERY;

D O I：

10.1080/10426507.2010.536189

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric Michael-type Friedel-Crafts (F-C) alkylations of indoles with nitroolefins catalyzed by a chiral H-8-BINOL-based phosphoric acid were investigated. The reactions took place very smoothly in the presence of only 5 mol-% of catalyst at room temperature to afford the desired F-C alkylation products in good yields and with moderate enantioselectivities.

引用

页码：2038 / 2046

页数：9

共 43 条

[41] BINAM and H8-BINAM-based chiral imines and Zn(OTf)2-catalyzed enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes
Yuan, Zhi-Liang
Lei, Zhi-Yu
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[42] A theoretical investigation into chiral phosphoric acid-catalyzed asymmetric Friedel-Crafts reactions of nitroolefins and 4,7-dihydroindoles: reactivity and enantioselectivity
Zheng, Chao
Sheng, Yi-Fei
Li, Yu-Xue
You, Shu-Li
[J]. TETRAHEDRON, 2010, 66 (15) : 2875 - 2880
[43] Enantioselective Friedel-Crafts type addition of indoles to nitro-olefins using a chiral hydrogen-bonding catalyst -: synthesis of optically active tetrahydro-β-carbolines
Zhuang, W
Hazell, RG
Jorgensen, KA
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (14) : 2566 - 2571

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